DE60118196T2 - USE OF A LIPONIC ACID (R) -ENANTIOMER IN COSMETICS AND DERMATOLOGY - Google Patents

Description

The The present invention relates to the use of lipoic acid, lipoic acid derivatives or salts thereof with an (R) -enantiomeric excess in cosmetic agents for rejuvenation and / or revitalizing the skin.

The human skin undergoes aging processes, being intrinsic Processes (chronoaging) and exogenous factors can. additionally for example B. also temporary or ongoing changes of the complexion, such as acne, oily or dry skin, keratoses, Rosaceae, photosensitive, inflammatory, erythematous, allergic or autoimmune reactive reactions such as dermatoses, photodermatoses and others whose exact causes and factors that influence them often only incomplete are understood.

To counting the exogenous factors For example, the sunlight or artificial radiation sources comparable spectrum, as well as compounds caused by the radiation can arise like undefined reactive, z. B. radical or ionic photoproducts. These factors include but also harmful or reactive compounds such as ozone, free radicals, such as the Hydroxyl radical, singlet oxygen and other reactive oxygen or nitrogen compounds, Cigarette smoke, natural and synthetic toxins, and others that have the natural physiology or morphology disturb the skin. For example, the influence of these factors leads to direct ones damage on the DNA of skin cells as well as the collagen, elastin or glycosaminoglycan molecules of the extracellular Matrix for the firmness of the skin are responsible. It can continue through the harmful ones influences but also to damage come to the cells of the skin itself. As a result, for example the ability to regenerate the skin is reduced. As a further consequence it can become inflammatory Reactions, including immunoregulatory compounds, how interleukins, prostaglandins and histamines play a role.

The Consequences of aging are dilution the skin, weaker Interlocking of epidermis and dermis, reduction of cell number as well of the supplying blood vessels. By the aging process leads to the formation of fine lines and wrinkles, the skin becomes leathery, yellowish and drooping, it occur pigmentary disorders on.

It It is known that exposure to sunlight leads to a large number of unwanted Effects in the skin: erythema, Photosensitization and immunological changes are examples of predominantly acute reactions while Photo aging and carcinogenesis represent long-term effects. there Oxidative processes also seem to play a role in photoaging to play. Furthermore, it is known that after irradiation of the skin matrix degrading Enzymes are induced and that this induction by low molecular weight Compounds, such. B. retinoic acids, can be reduced. Another effect of UV radiation is the appearance of sunburn cells in the skin. This can be necrotic Processes that induce an inflammatory reaction occur or reinforce.

The same factors also affect hair, where it also becomes one damage can come. The hair becomes brittle, less elastic and lackluster; the surface structure the hair is damaged.

At the properties of cosmetic or dermatological agents Therefore, a large number of demands are made. That's the way they should be among others z. B. radical scavenging, antioxidant, anti-inflammatory or moisturizing, the activity of matrix-degrading enzymes prevent or reduce and / or re-synthesis of collagen, Regulate elastin and / or proteoglycans.

It is known to have antioxidant compounds in dermatological or cosmetic preparations for protection against deterioration. About that can out They are also used to oxidize harmful or unwanted Processes that occur in human or animal skin, too reduce. The skin is permanently exposed to oxidative stress, partly from the external environment of the Skin is derived in part but also based on endogenous factors. The skin's own protective mechanisms are usually not sufficient to completely prevent oxidative processes in the skin, so that these processes are expected to make a significant contribution to skin aging, but also contribute to general or pathological changes of the skin.

The DE-A-197 39 349 suggests before, in support the endogenous protective mechanisms of the skin antioxidant ingredients to add to cosmetic and dermatological preparations. The However, the effect achieved is still in need of improvement.

α-lipoic acid (1,2-dithiacyclopentane-3-valeric acid) is used as a coenzyme in the oxidative decarboxylation of α-keto acids and is found in the form of its (R) -enantiomer in almost every cell plant and animal organisms.

anti-inflammatory, analgesic and cytoprotective properties as well as their antioxidant The lipoic acid is effective to an interesting drug for pharmacy, cosmetics, nutrition science and adjacent areas (Biothiols in Health and Disease, ed Packer L. and Cadenas E., Marcel Dekker Inc., New York, Basel, Hong Kong). Stoll et al. in Pharmacology Biochemistry and Behavior, Vol. 46, p. 799-805 (1993) and Ann. NY Acad. Sci., Vol. 717, pp. 122-128 (1994), that lipoic acid long-term memory old mice or cognitive abilities of rodents can improve. T.M. Hagen et al. describe in FASEB journal, Vol. 13, pp. 411-418 (1999) found a revitalizing effect of orally administered lipoic acid old rats.

The EP-A-0 572 922 describes the use of α-lipoic acid and derivatives thereof in Combination with a vitamin for the production of medicines with analgesic, antiphlogistic, antidiabetic, cytoprotective, antiulcerative, antinecrotic, neuroprotective, detoxifying, anti-ischemic, Liver function-regulating, antiallergic, immunostimulating like antioncogenic effect. It is quite generally pointed out that for various of these applications make an optically pure isomer more effective can be as the racemate.

The EP-A-0 427 247 describes pharmaceuticals and processes for their preparation, the R-α-lipoic acid or S-α-lipoic acid or their pharmaceutically acceptable salts. The Arnzneimittel have a cytoprotective effect and are suitable for controlling Pain and inflammatory diseases.

The WO-A-97/10808 describes a method of treatment or prevention of skin damage, especially by inflammation and aging, with a topical composition on the damaged skin areas applying, the lipoic acid or a derivative thereof. The use of lipoic acid and lipoic acid derivatives with an (R) -enantiomeric excess is not described. In addition, the compositions described are in terms of their effect, in particular when remedy already incurred skin damage still in need of improvement.

Of the The present invention is based on the object, an active ingredient for use in skin or hair cosmetics or for manufacture of dermatics available to deliver. These cosmetics and dermatics should preferably be and hair damage and / or unwanted changes to prevent the appearance of the skin. They should be especially for treatment of already incurred skin and hair damage or unwanted changes the appearance of the skin are suitable.

Surprisingly open the use of lipoic acid, lipoic acid derivatives or salts thereof with an (R) -enantiomeric excess, an effective prevention and treatment option such disorders.

object The invention therefore relates to the use of lipoic acid, lipoic acid derivatives or cosmetically acceptable salts thereof, each with an (R) -enantiomeric excess (ee) of at least 40%, in cosmetic preparations for rejuvenation and / or revitalization of the skin.

Erfindungsgemäß wird die (R)-5-(1,2-Dithiolan-3-yl)valeriansäure der Formel II

oder Derivate oder Salze davon in Reinform oder in Form von Gemischen optischer Isomere mit einem (R)-Enantiomeren-Überschuss (ee) von mindestens 40% eingesetzt.The term "lipoic acid" denotes according to the invention 5- (1,2-dithiolan-3-yl) valeric acid, also called thioctic acid, thioctic acid or thioctic acid, of the formula I.

According to the invention, the (R) -5- (1,2-dithiolan-3-yl) valeric acid of the formula II

or derivatives or salts thereof used in pure form or in the form of mixtures of optical isomers with an (R) -enantiomeric excess (ee) of at least 40%.

Of the Enantiomeric excess (enantiomeric excess, ee) is given by the following formula: ee [%] = (R - S) / (R + S) × 100. R and S are the descriptors of the CIP system for the two enantiomers and give the absolute configuration at the asymmetric C (5) atom. The enantiomerically pure compound (ee = 100%) is also called homochiral Called connection.

It can also mixtures of lipoic acid, used at least one derivative and / or at least one salt with an (R) enantiomeric excess of at least 40% is achieved.

Preferably is the (R) -enantiomeric excess at least 80%, in particular at least 98%.

To lipoic acid derivatives belong in particular metabolites of lipoic acid, ie especially dihydrolipoic acid. When Other metabolites are lipoamide, lipoyl lysine, di-6,8-bis-norlipoic acid and Tetranorlipoic acid too call. The designs to lipoic acid belong accordingly also the respective optical isomers of the derivatives thereto.

The cosmetically and pharmaceutically acceptable salts of lipoic acid or Lipoic acid derivatives are in the present case preferably base addition salts.

The base addition salts include salts of lipoic acid or lipoic acid derivatives with inorganic bases, for example metal hydroxides or carbonates of alkali metals, alkaline earth metals or transition metals, or with organic bases, for example basic amino acids, such as arginine and lysine, amines of the formula NR ³ R ⁴ R ⁵ , in which the radicals R ³ , R ⁴ and R ^{5 may be} identical or different and denote hydrogen or hydroxy-optionally substituted C ₁ -C ₄ -alkyl, in particular methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec- Butyl or tert-butyl or mono- and diethanolamine, 1-amino-2-propanol or 3-amino-1-propanol, C ₂ -C ₆ -alkylenediamines, such as ethylenediamine or hexamethylenetetraamine, saturated cyclic amines having 4 to 6 ring carbon atoms, such as piperidine, piperazine, pyrrolidine and morpholine, as well as other organic bases such as N-methylglucamine, creatine and tromethamine.

Prefers For example, salts with inorganic bases, e.g. B. Na, K, Mg, Ca, Zn, Cr and Fe salts.

Lipoic acid and their derivatives and salts with the optical purity described above are advantageously suitable for the prevention and treatment of damage on keratinous surfaces, d. H. Skin and skin appendages, such. Hair, nails etc., of individuals, preferably mammals, especially people, pets or pets. The use can doing so in cosmetic products such as personal care products, decorative Cosmetics etc. take place which are usually not prescription are.

The Treatment according to the invention The diseased skin may be due to individual disorders (abnormalities, or morbid Conditions) be directed, it can but also if desired several possibly causative interconnected anomalies by an inventive means, which optionally contains a drug combination treated become.

cosmetic and dermatological preparations based on (R) -enantiomer-enriched or pure lipoic acid, Derivatives and / or salts thereof provide effective protection oxidative processes, by radiation or reactive compounds caused processes, from damage caused by such processes caused directly or indirectly. They are advantageous for the treatment of cosmetic or dermatological changes on skin and hair, such as. Skin aging, loss of skin moisture, the loss of skin elasticity, the formation of wrinkles or wrinkles or pigmentation disorders or Age spots.

Particularly preferred is (R) -enantiomer-enriched or pure lipoic acid for rejuvenation and / or revitalization of the skin. Advantageously, as a rule, energizing effects can also be observed. In particular, (R) -enantiomer-enriched or pure lipoic acid has a positive effect on mitochondrial function. Surprisingly, oxidative damage to the skin is not only prevented but already existing damage can be eliminated, at least in part. In this case, improvements in the moisture value and / or the elasticity of the skin are recorded. The application of (R) -enantiomer-enriched or pure lipoic acid increases the new synthesis of collagen and / or elastin. This generally leads to a, at least partial, smoothing of wrinkles, the complexion looks radiant and fresher. In general, with the mentioned beneficial effects also a positive subjek tive feeling of having overall "youthful" skin.

Enriched (R) lipoic acid Formulations are also advantageous for the treatment, the Care and cleansing of the skin or hair and can be used as a make-up product to serve in cosmetics. They preferably contain 0.001% by weight to 30 wt .-% of the active ingredient. The composition is aimed z. B. according to the penetration properties of the active substance the stratum corneum and its ability to to form a depot in the skin.

To a preferred embodiment the application according to the invention takes place of (R) -enantiomer-enriched or pure lipoic acid, derivatives and / or salts thereof advantageous by regular application, for. In Form of a cosmetic or dermatological preparation, via a Time span. This depends on the desired goal, d. H. the time span can be over extend the lifetime of the user, preferably via a Time span up to three months, more preferably over one week up to two months, when the goal is to build a depot in the skin. For one After-sun application is considered as application period in the sense of the invention the one-time application, but preferably a period of at least one day, more preferably over three days to three months, especially preferred over one to two weeks.

It is recommended for the purposes of the invention, the cosmetic or dermatological preparation of the lipoic acid in an amount of 0.1 mg / cm ² to 2 mg / cm ² , between once a week and 4 to 5 times a day, preferably 3 times a week until 3 times daily, more preferably one to two times a day, topically applied. Active ingredient amounts and proportions refer to the active ingredient, so that for salts and derivatives, a corresponding conversion has to be made.

For after-sun Applications provided dosage forms of lipoic acid as well possibly additional Active ingredients have advantageous penetration properties, the one allow rapid penetration of the substance into the skin. On the other hand is for applications with "preconditioning" character a fast penetration usually unimportant, but the ability to depot in the skin build up, beneficial.

Surprisingly is in the inventive application an effective treatment, but also prevention of prematurely aged Skin (eg, wrinkles, age spots, telangiectasias, pigmentation disorders) and / or Prematurely aged skin appendages, radiation-related skin damage or radiation-related negative changes in the skin and / or dermal appendages, environmental (ozone, free radicals, singlet oxygen, reactive oxygen or nitrogen compounds, cigarette smoke, Toxins) Skin damage or environmental adverse skin changes and / or dermal appendages, photosensitive, inflammatory, erythematous, allergic or autoimmune reactive changes skin and / or skin appendages (especially acne, greasy or dry skin, keratoses, rosaceae, dermatoses, atopic Eczema, seborrheic dermatitis, photodermatoses, polymorphic photodermatosis), deficient, sensitive or hypoactive states skin and / or skin appendages, itching, dry skin conditions and Horny layer barrier disorders and / or hair loss and reduced hair growth possible.

The use according to the invention of (R) -enantiomer-enriched or pure lipoic acid, derivatives and / or salts thereof in cosmetic and dermatological preparations but also serves as a surprise and unpredictable way to calm down more sensitive and irritated skin, regulation of collagen, hyaluronic acid, elastin synthesis, Stimulation of DNA synthesis, especially in deficit or hypoactive skin conditions, Regulation of transcription and translation of matrix-degrading enzymes, in particular the matrix metalloproteinases, increase cell renewal and Regeneration of the skin, enhancement of the skin's own protective and repair mechanisms for DNA, Lipids and / or proteins as well as for pre- and post-treatment in surgical Interventions, in particular to counteract skin irritation and the regeneration processes to promote the injured skin.

to use according to the invention are the cosmetic and dermatological preparations in the for cosmetics usual Applied to the skin and / or hair in sufficient quantity.

For example, the (R) -enantiomer-enriched or pure lipoic acid and / or a derivative or salt thereof in skin cleansing cosmetics such as bar soaps, toilet soaps, core soaps, transparent soaps, luxury soaps, de-soaps, cream soaps, baby soaps, skin soaps, abrasive soaps, syndets , liquid soaps, pasty soaps, soft soaps, washing pastes, liquid washing, shower and bath preparations such as washing lotions, Duschbä countries, shower gels, bubble baths, cream bubble baths, oil baths, Ba dextracts, scrub preparations, in-situ products, shaving foams, shaving lotions, shaving creams used.

Farther is it suitable for skin cosmetic preparations such as W / O or O / W skin and body creams, Day and night creams, eye creams, sunscreen, after sun Products, Hand Care Products, Face Creams, Multiple Emulsions, Jellies, microemulsions, liposome preparations, nosome preparations, anti-wrinkle creams, Face Oil, Lipogels, sports gels, moisturizing creams, bleaching creams, vitamin creams, Skin lotions, body lotions, vials, after shave lotions, pre-shaves, Moisturizing lotions, tanning lotions, Cellulite creams, depigmenting agents, massage preparations, Body powder, Facial Toner, Facial Masks, Deodorants, Antiperspirants, Nose Strips, Anti-Acne, Repellent, Shaving, Hair Removal, Intimate care products, foot care products, Baby care products and others.

In addition, can the lipoic acid and / or a derivative or salt thereof in hair care cosmetics hair conditioners, hair lotions, hair conditioners, hair emulsions, top fluids, Leveling agent for Perms, hot oil treatment preparations, conditioners, setting lotions, Shampoos, hair tinting and hair dyes, Hair sprays, hair lotions, Gloss sprays, hair brillantines, hair styling products, hair lotions, alopecia skin care products and others are used.

Lipoic acid and / or a derivative or salt thereof are also suitable for use in cosmetic preparations for the decorative cosmetics, for example as make-up, powder, rouge, eye shadow, Eyeliner pencils, eyeliner, eyefoundation cream, lipsticks, eyebrow pencils, Contour pencil, masking pens, theatrical make-up, mascara, and eyelashes Eyelash tinting products, Make-up removal products and others.

The cosmetic, hygienic, dermatological or pharmaceutical Preparations can depending on the application as spray (pump spray or aerosol), foam, Gel, gel spray, lotion, cream, mousse, ointment, suspensions or powder be prepared.

It is also beneficial lipoic acid and / or a derivative or salt thereof, optionally with further active ingredients in encapsulated form, z. B. as cellulose encapsulation, in gelatin, with polyamides, in niosomes, wax matrices, with cyclodextrins or liposomally encapsulated.

The Preparations can contain cosmetic excipients, such as those commonly used in such preparations be used, for. As preservatives, bactericides, perfumes, substances for preventing foaming, Dyes, pigments, thickeners, surface-active substances, emulsifiers, emollients Substances, lubricants, fats, oils, waxes or other common ingredients a cosmetic or dermatological formulation such as alcohols, Polyols, polymers, foam stabilizers, solubilizers, electrolytes, organic acids, organic solvents or silicone derivatives.

The Preparations can additionally to the said active ingredients contain further compounds which antioxidant, as radical scavenger, Skin moisturizing or moisturizing, anti-erythematous, anti-inflammatory or have an anti-allergic effect in order to supplement or enhance their effect. Especially can selected these compounds are selected from the group of vitamins, plant extracts, α- and β-hydroxy acids, ceramides, anti-inflammatory, antimicrobial or UV-filtering substances, as well as their derivatives and mixtures thereof.

Advantageously, the antioxidants are selected from amino acids (eg glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (eg urocaninic acid) and derivatives thereof, peptides such as D, L-carnosine, D-carnosine, L-carnosine and L-carnosine. Carnosine and its derivatives (eg anserine), carotenoids, carotenes (eg α-carotene, β-carotene, lycopene) and derivatives thereof, chlorogenic acid and its derivatives, aurothioglucose, propylthiouracil and other thiols (eg. Thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and Glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (eg buthionine sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta, hexa, heptathionine sulfoximine) in very low tolerances doses (eg. Pmol to mmol / kg), furthermore (metal) chelators (eg α-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid, Bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (eg B. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin E acetate), vitamin A and derivatives (vitamin A palmitate), as well as coniferyl benzoate of benzoin, rutinic acid and its derivatives, butyl hydroxytoluene, butylhydroxyanisole, nordihydroguaiacetic acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, sesamol, sesamolin, zinc and its derivatives (eg ZnO, ZnSO ₄ ), selenium and its derivatives (eg selenomethionine) , Stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the inventively suitable derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances.

The Antioxidants can used alone or in the form of mixtures. The amount of the Antioxidants in the preparations, alone or in combination, is preferably from 0.001 to 30% by weight, based on the total weight of Preparation.

Prefers also contain the preparations Substances that absorb UV radiation in the UV-B and / or UV-A range. Suitable UV filters are z. B. 2,4,6-triaryl-1,3,5-triazines in which the aryl groups may each bear at least one substituent, the preferably selected is hydroxy, alkoxy, especially methoxy, alkoxycarbonyl, especially Methoxycarbonyl and ethoxycarbonyl, and mixtures thereof. Suitable are also 4-aminobenzoic acid esters, wherein the amino group is optionally alkylated or alkoxylated can be. Also includes z. N, N-dimethyl-4-aminobenzoic acid isooctyl ester. Suitable are also 2-hydroxybenzoic acid esters, such as B. the isooctyl ester. Further suitable UV filters are 2,4,6-trianilin (o-carbo-2'-ethylhexyl-1'-oxy) -1,3,5-triazine, 3-imidazol-4-yl-acrylic acid and their ethyl ester, menthyl o-aminobenzoate, glyceryl p-aminobenzoate, 2,2'-dihydroxy-4-methoxybenzophenone (Dioxybenzone), 2-hydroxy-4-methoxy-4-methylbenzophenone (mexenone), Triethanolamine salicylate, dimethoxyphenylglyoxalic acid, 3- (4'-sulfo) benzylidene-bornan-2-one and its Salts, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2,2'-methylene-bis [6- (2H-benzotriazol-2-yl-4- (1,1,3,3-tetramethylbutyl) phenol], 2,2 '- (1,4-phenylene) -bis-1 H-benzimidazole-4,6-disulfonic acid and its sodium salt, 2,4-bis [4- (2-ethylhexyloxy) -2-hydroxy] phenyl-6- (4-methoxyphenyl) - (1,3,5) -triazine, 3- (4- methylbenzylidene) camphor, 4-bis (polyethoxy) paraaminobenzoic acid polyethoxyethyl ester, 2,4-dihydroxybenzophenone and / or 2,2'-dihydroxy-4,4'-dimethoxybenzophenone-5,5'-disodium sulfonate.

The List of said UV filters, in combination with the active compound combinations according to the invention can be used should of course not limiting.

The Total amount of filter substances is usually 0.1 to 30 Wt .-%, preferably 0.5 to 15 wt .-%, in particular 1 to 10 wt .-%, based on the total weight of the preparations to cosmetic Preparations available to put the skin in front of the entire area of the ultraviolet Protect radiation.

If a lipid phase is used, it is preferably selected from mineral oils, mineral waxes, branched and / or unbranched hydrocarbons and waxes, triglycerides of saturated and / or unsaturated, branched and / or unbranched C ₈ -C ₂₄ -alkanecarboxylic acids; synthetic, semi-synthetic or natural oils such as olive oil, palm oil, almond oil or mixtures; Oils, fats or waxes; Esters of saturated and / or unsaturated, branched and / or unbranched C ₃ -C ₃₀ -alkanecarboxylic acids and saturated and / or unsaturated, branched and / or unbranched C ₃ -C ₃₀ -alcohols, esters of aromatic carboxylic acids and saturated and / or unsaturated branched and / or unbranched C ₃ -C ₃₀ -alcohols, for example isopropyl myristate, isopropyl stearate, hexyldecyl stearate, oleyl oleate; synthetic, semi-synthetic and natural mixtures of the aforementioned esters, such as jojoba oil, alkyl benzoates or silicone oils such as cyclomethicone, dimethylpolysiloxane, diethylpolysiloxane, octamethylcyclotetrasiloxane and mixtures thereof or dialkyl ethers.

If an aqueous phase is used, it optionally additionally contains a water-miscible solvent, such as C ₁ to C ₁₀ , preferably C ₁ to C ₅ alcohols, diols or polyols, and their ethers, preferably ethanol, isopropanol, propylene glycol , Glycerine, ethylene glycol monoethyl ether etc.

When Emulsifiers are preferably known W / O and O / W emulsifiers such as polyglycerol esters, sorbitan esters or partially esterified glycerides into consideration.

When suitable solubilizers are in particular ethoxylated sorbitan esters, ethoxylated Lanolinalkohole and ethoxylated castor oil to call.

Usual native and synthetic thickening agents or gelling agents in the formulations are crosslinked polyacrylic acids and their derivatives, polysaccharides such as xanthan gum or alginates, Carboxymethylcellulose or hydroxycarboxymethylcellulose, hydrocolloids such as gum arabic or montmorillonite minerals such as bentonite or Fatty alcohols, polyvinyl alcohol and polyvinylpyrrolidone.

When Propellant for Aerosols come the usual Propellants in question, for example propane, butane, pentane, dimethyl ether and other.

• I) Liponsäure, Liponsäurederivate oder pharmazeutisch akzeptable Salze davon, jeweils mit einem (R)-Enantiomeren Überschuss (ee) von mindestens 40%,
• II) gegebenenfalls wenigstens einen weiteren kosmetischen Wirkstoff, und
• III) einen kosmetisch akzeptablen Träger.

The invention provides the use according to claims 1 to 3 in the form of a cosmetic composition containing

• I) lipoic acid, lipoic acid derivatives or pharmaceutically acceptable salts thereof, each having an (R) -enantiomeric excess (ee) of at least 40%,
• II) optionally at least one further cosmetic active ingredient, and
• III) a cosmetically acceptable carrier.

Preferably the agents contain components I in an amount of 0.001 to 30 wt .-%, in particular 0.01 to 25 wt .-%, based on the Total weight of the agent.

Regarding suitable Components II) and III), reference is made to the above.

• i) Liponsäure, Liponsäurederivaten oder pharmazeutisch akzeptablen Salzen davon, jeweils mit einem (R)-Enantiomeren Überschuss (ee) von mindestens 40%,
• ii) gegebenenfalls wenigstens einen weiteren Wirkstoff, und
• iii) eine Formulierungsgrundlage,

gegebenenfalls zusammen mit Instruktionen für die therapeutische Verwendung von Liponsäure, Liponsäurederivaten oder pharmazeutisch akzeptablen Salzen davon, jeweils mit einem (R)-Enantiomeren Überschuss (ee) von mindestens 40%.Another object of the present invention are means in the form of a commercial pack with at least one agent based on

• i) lipoic acid, lipoic acid derivatives or pharmaceutically acceptable salts thereof, each having an (R) -enantiomeric excess (ee) of at least 40%,
• ii) optionally at least one further active ingredient, and
• iii) a formulation basis,

optionally together with instructions for the therapeutic use of lipoic acid, lipoic acid derivatives or pharmaceutically acceptable salts thereof, each having an (R) -enantiomeric excess (ee) of at least 40%.

It is understood that inventive commercial packs also more Preparations, especially active ingredient-containing formulations, as well as comprehensive, also over contain the above-mentioned content instructions can.

Beispiel 1 Soft Skin Fluid Gew.-% Ceteareth-6 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) und Stearylalkohol 2,50 Ceteareth-25 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) 2,50 Hydrierte Kokosfett-Glyceride 1,50 Polyethylenglycol (40 EO-Einheiten)-Dodecylglycolcopolymer 3,00 Dimethicon 3,00 Phenethyldimethicon 2,00 Cyclomethicon 1,00 Cetearyloctanoat 5,00 Avocadoöl 1,00 Süßmandelöl 2,00 Weizenkeimöl 0,80 Panthenol USP 1,00 Phytantriol 0,20 Tocopherylacetat 0,30 Propyleneglycol 5,00 Parfum q.s. Konservierungsstoffe q.s. Liponsäure (>98% ee) q.s. Wasser 69,20 Beispiel 2 Schützende Handcreme Gew.-% Cetearylalkohol 1,00 Glycerylstearat 1,50 Stearylalkohol 1,50 Cetylpalmitat 2,00 Tocopherylacetat 0,50 Dimethicon 8,00 Ceteareth-6 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) und Stearylalkohol 3,00 Octylmethoxycinnamat 5,00 Propylenglycol 8,00 Panthenol 1,00 Nachtkerzenöl 3,00 ethoxyliertes hydriertes Rizinusöl (7 EO) 6,00 Glyceryloleat 1,00 Phenethyldimethicon 3,00 Bienenwachs 1,50 Johannisbrot-Gummi 0,80 Silkpowder 0,80 Konservierungsstoffe q.s. Parfum q.s. Borax 0,10 Liponsäure (>98% ee) q.s. Wasser 52,30 Beispiel 3 Sonnenpflege-Lotion Gew.-% ethoxiliertes hydriertes Rizinusöl (7 EO) 6,00 ethoxiliertes hydriertes Rizinusöl (40 EO) 0,50 Isopropylpalmitat 7,00 Polyethylenglycol (40 EO)-Dodecylglycolcopolymer 2,00 Jojobaöl 3,00 Magnesiumstearat 0,60 Octylmethoxycinnamat 8,00 C12-15-Alkylbenzoat 5,00 Titandioxid 4,00 Propylenglycol 5,00 EDTA 0,20 Konservierungsstoffe q.s. Wasser 57,20 Natriumascorbylphosphat 1,00 Tocopherylacetat 0,50 Liponsäure (>98% ee) q.s. Parfum q.s. Beispiel 4 Multiple Emulsion Gew.-% Mineralöl 7,50 Cetearyloctanoat 2,50 Aluminiumstearat 0,25 Magnesiumstearat 0,25 Microcristallines Wax H 0,50 Cetearylalkohol 1,00 Lanolinalkohol 1,50 Mineralalkohol und Lanolinalkohol 1,50 ethoxiliertes hydriertes Rizinusöl (7 EO) 0,75 Polyethylenglycol (40 EO)-Dodecyl glycolcopolymer 2,00 Ceteareth-6 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) und Stearylalkohol 2,00 Ceteareth-25 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) 2,00 Trilaureth-4-phosphat 1,00 Hydroxyethylcellulose 0,20 Propylenglycol 7,50 Magnesiumsulfat 0,25 Liponsäure (>98% ee) q.s. Wasser 69,30 Beispiel 5 Microemulsion Gew.-% Ceteareth-25 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) 13,00 Glycerylcocoat (7 EO) 20,00 Octyldodecanol 5,00 Konservierungsstoffe q.s. Liponsäure (>98% ee) q.s. Wasser 62,00 Beispiel 6 Liposomengel Gew.-% ethoxiliertes hydriertes Rizinusöl (40 EO) 1,00 Bisabolol rac. 0,10 Propylenglycol 8,00 Panthenol 0,50 Wasser und Tocopherylacetat und Polysorbat 80 und Capryl/Caprin-Triglycerid und Lecithin 3,00 Konservierungsstoffe q.s. Parfum q.s. Carbomer 0,50 Liponsäure (>98% ee) q.s. Triethanolamin 0,70 Wasser 86,30 Beispiel 7 Blunted Oil Gel Gew.-% Siliciumdioxid 5,00 Dimethicon 10,00 Cetearyloctanoat 40,00 Capryl/Caprin-Triglycerid 8,00 Phenethyldimethicon 2,00 Mineralöl 28,50 Süßmandelöl 5,00 Phytantriol 0,30 Liponsäure (>98% ee) q.s. Tocopherol 0,50 Parfum 1,00 Beispiel 8 Öl Gel Gew.-% Siliciumdioxid 5,00 Dimethicon 10,00 Cetearyloctanoat 30,00 Capryl/Caprin-Triglycerid 10,00 Isopropylmyristat 5,00 Phenethyldimethicon 5,00 Mineralöl 28,20 Jojobaöl 5,00 Phytantriol 0,30 Liponsäure (>98% ee) q.s. Tocopherol 0,50 Parfum 1,00 Beispiel 9 pflegender Sonnenschutz Gew.-% Bienenwachs 12,00 Hydrierte Kokosfett-Glyceride 5,00 Rizinusöl 40,00 Isopropylpalmitat 10,00 Mineralöl 10,00 Candellilawachs 8,00 Phenethyldimethicon 5,00 Liponsäure (>98% ee) q.s. Petrolat 5,00 3-Benzophenon 5,00 Beispiel 10 kühlender Body Splash Gew.-% Ethoxyliertes hydriertes Rizinusöl (40 EO) 2,00 Menthyllactat 0,20 Alkohol 5,00 Glycerylcocoat (7 EO) 2,00 Witch Hazel 5,00 Allantoin 0,10 Bisabolol rac. 0,20 Propylenglycol 5,00 Panthenol USP 0,50 Milchsäure (80%ig) 0,20 Liponsäure (>98% ee) q.s. Parfum q.s. Wasser 79,80 Beispiel 11 Make-up Gew.-% Ceteareth-6 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) und Stearylalkohol 9,00 Dimethicon 5,00 Cetearyloctanoat 8,00 Macadamianussöl 5,00 Propylenglycol 5,00 Wasser 53,00 Sicovit White E 171 8,00 Sicomet Brown 70 13E 3717 2,00 Liponsäure (>98% ee) q.s. Parfum q.s. 3-Benzophenon 5,00 Beispiel 12 Flüssig-Make-up Gew.-% Ceteareth-6 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) und Stearylalkohol 7,00 Ceteareth-25 5,00 Dimethicon 5,00 Cetearyloctanoat 8,00 Macadamianussöl 5,00 Propylenglycol 5,00 Wasser 53,00 Sicovit Weiss E 171 8,00 Sicomet Braun 70 13E 3717 1,00 Liponsäure (>98% ee) q.s. Parfum q.s. 3-Benzophenon 5,00 Beispiel 13 Sonnenpflege-Öl Gew.-% Cetearyloctanoat 40,00 Capryl/Caprin-Triglyceride 28,70 Nachtkerzenöl 3,00 Macadamianussöl 5,00 Isopropylpalmitat 5,00 Dimethicon 3,00 Octylmethoxycinnamat 8,00 Octocrylen 5,00 3-Benzophenon 2,00 Phytantriol 0,10 Liponsäure (>98% ee) q.s. Tocopherylacetat 0,20 Parfum q.s. Beispiel 14 Gesichts-Tiefenreiniger Gew.-% Wasser 65,60 Cocoamidopropylbetain 5,00 Natrium-Cocoat, hydrolisiertes tierisches Protein 8,00 Ethoxyliertes hydriertes Rizinusöl (40 EO) 2,00 Polyquaternium-44 7,70 Bisabolol rac. 0,20 Panthenol 1,00 Parfum 0,50 Hydroxyethylcellulose 2,00 Liponsäure (>98% ee) q.s. Propylenglycol 5,00 Jojobawachs 3,00 Beispiel 15 Conditioner Gew.-% Ceteareth-6 und Stearylalkohol 2,00 Ceteareth-25 (Umsetzungsprodukt aus Fettalkohol und Ethylenoxid) 1,00 Cetearyloctanoat 6,00 Ceteareth-3 2,00 Cetearylalkohol 6,00 Phytantriol 1,00 Propylenglycol 5,00 Polyquaternium-11 5,00 Panthenol 1,00 Retinylacetat 0,50 Parfum q.s. Liponsäure (>98% ee) q.s. Konservierungsstoffe q.s. Wasser 70,50 Beispiel 16 Haarwachs Gew.-% Polyethylenglycol-6 30,00 Polyethylenglycol-75 45,00 flüssiges Paraffinöl 0,50 Ethoxyliertes hydriertes Rizinusöl (40 EO) 1,00 Glycerin 15,00 3-Benzophenon 2,00 Phytantriol 0,10 Liponsäure (>98% ee) q.s. Parfum q.s. Wasser 6,40 Beispiel 17 Anti-Schuppen Haartonikum Gew.-% Alkohol 45,00 Aloe Vera (10fach Konz.) 1,00 Panthenol 1,00 Tocopherylacetat 0,50 Ethoxyliertes hydriertes Rizinusöl (40 EO) 0,50 Allantoin 0,10 Hydrolysiertes tierisches Protein 1,50 1-(4-Chlorphenoxy)-1-(1H-imidazolyl)-3,3-dimethyl-2-butanon 0,30 Parfum 0,10 Liponsäure (>98% ee) q.s. Wasser 50,00 Beispiel 18 Fuß-Deospray Gew.-% Ethoxyliertes hydriertes Rizinusöl (40 EO) 0,80 Alkohol 20,00 Farnesol 0,12 Menthyllactat 0,08 1,2-Propylenglycol 3,20 4-Benzophenon 1,20 Glycerylcocoat (7 EO) 0,80 Parfum q.s. Liponsäure (>98% ee) q.s. Wasser 13,80 Butan 60,00 Beispiel 19 Haarspray Gew.-% Aminomethylpropanol 0,40 Dimethiconcopolyol 0,030 Alkohol 43,67 Pentan 14,20 Acrylat/Acrylamid-Copolymer 3,40 Parfum q.s. Liponsäure (>98% ee) q.s. Butan 2,40 Isobutan 35,90 The invention will be explained in more detail with reference to the following, non-limiting examples. Examples of cosmetic preparations

Example 1 Soft Skin Fluid Wt .-% Ceteareth-6 (reaction product of fatty alcohol and ethylene oxide) and stearyl alcohol 2.50 Ceteareth-25 (reaction product of fatty alcohol and ethylene oxide) 2.50 Hydrogenated coconut fat glycerides 1.50 Polyethylene glycol (40 EO units) -Dodecylglycolcopolymer 3.00 dimethicone 3.00 Phenethyldimethicon 2.00 cyclomethicone 1.00 cetearyl 5.00 avocado oil 1.00 sweet almond oil 2.00 Wheat germ oil 0.80 Panthenol USP 1.00 phytantriol 0.20 tocopheryl acetate 0.30 propyleneglycol 5.00 Perfume qs preservatives qs Lipoic acid (> 98% ee) qs water 69.20 Example 2 Protective hand cream Wt .-% cetearyl 1.00 glyceryl stearate 1.50 stearyl 1.50 cetyl palmitate 2.00 tocopheryl acetate 0.50 dimethicone 8.00 Ceteareth-6 (reaction product of fatty alcohol and ethylene oxide) and stearyl alcohol 3.00 octyl 5.00 propylene glycol 8.00 panthenol 1.00 Evening primrose oil 3.00 ethoxylated hydrogenated castor oil (7 EO) 6.00 glyceryl 1.00 Phenethyldimethicon 3.00 beeswax 1.50 Locust bean gum 0.80 Silkpowder 0.80 preservatives qs Perfume qs borax 0.10 Lipoic acid (> 98% ee) qs water 52,30 Example 3 Sun Care Lotion Wt .-% ethoxylated hydrogenated castor oil (7 EO) 6.00 ethoxylated hydrogenated castor oil (40 EO) 0.50 isopropyl palmitate 7.00 Polyethylene glycol (40 EO) -Dodecylglycolcopolymer 2.00 jojoba oil 3.00 magnesium stearate 0.60 octyl 8.00 C12-15 alkyl benzoate 5.00 Titanium dioxide 4.00 propylene glycol 5.00 EDTA 0.20 preservatives qs water 57.20 sodium ascorbyl 1.00 tocopheryl acetate 0.50 Lipoic acid (> 98% ee) qs Perfume qs Example 4 Multiple emulsion Wt .-% mineral oil 7.50 cetearyl 2.50 aluminum stearate 0.25 magnesium stearate 0.25 Microcrystalline wax H 0.50 cetearyl 1.00 lanolin 1.50 Mineral alcohol and lanolin alcohol 1.50 ethoxylated hydrogenated castor oil (7 EO) 0.75 Polyethylene glycol (40 EO) dodecyl glycolcopolymer 2.00 Ceteareth-6 (reaction product of fatty alcohol and ethylene oxide) and stearyl alcohol 2.00 Ceteareth-25 (reaction product of fatty alcohol and ethylene oxide) 2.00 Trilaureth 4-phosphate 1.00 hydroxyethyl 0.20 propylene glycol 7.50 magnesium sulfate 0.25 Lipoic acid (> 98% ee) qs water 69.30 Example 5 Microemulsion Wt .-% Ceteareth-25 (reaction product of fatty alcohol and ethylene oxide) 13,00 Glyceryl cocoate (7 EO) 20.00 octyldodecanol 5.00 preservatives qs Lipoic acid (> 98% ee) qs water 62,00 Example 6 Liposome gel Wt .-% ethoxylated hydrogenated castor oil (40 EO) 1.00 Bisabolol rac. 0.10 propylene glycol 8.00 panthenol 0.50 Water and tocopheryl acetate and polysorbate 80 and caprylic / capric triglyceride and lecithin 3.00 preservatives qs Perfume qs Carbomer 0.50 Lipoic acid (> 98% ee) qs triethanolamine 0.70 water 86.30 Example 7 Blunted Oil Gel Wt .-% silica 5.00 dimethicone 10.00 cetearyl 40,00 Caprylic / capric triglyceride 8.00 Phenethyldimethicon 2.00 mineral oil 28.50 sweet almond oil 5.00 phytantriol 0.30 Lipoic acid (> 98% ee) qs tocopherol 0.50 Perfume 1.00 Example 8 Oil Gel Wt .-% silica 5.00 dimethicone 10.00 cetearyl 30.00 Caprylic / capric triglyceride 10.00 isopropyl 5.00 Phenethyldimethicon 5.00 mineral oil 28,20 jojoba oil 5.00 phytantriol 0.30 Lipoic acid (> 98% ee) qs tocopherol 0.50 Perfume 1.00 Example 9 nourishing sunscreen Wt .-% beeswax 12,00 Hydrogenated coconut fat glycerides 5.00 castor oil 40,00 isopropyl palmitate 10.00 mineral oil 10.00 candelilla 8.00 Phenethyldimethicon 5.00 Lipoic acid (> 98% ee) qs petrolatum 5.00 3-Benzophenone 5.00 Example 10 Cooling Body Splash Wt .-% Ethoxylated hydrogenated castor oil (40 EO) 2.00 menthyl 0.20 alcohol 5.00 Glyceryl cocoate (7 EO) 2.00 Witch Hazel 5.00 allantoin 0.10 Bisabolol rac. 0.20 propylene glycol 5.00 Panthenol USP 0.50 Lactic acid (80%) 0.20 Lipoic acid (> 98% ee) qs Perfume qs water 79,80 Example 11 Make-up Wt .-% Ceteareth-6 (reaction product of fatty alcohol and ethylene oxide) and stearyl alcohol 9.00 dimethicone 5.00 cetearyl 8.00 Macadamianussöl 5.00 propylene glycol 5.00 water 53,00 Sicovit White E 171 8.00 Sicomet Brown 70 13E 3717 2.00 Lipoic acid (> 98% ee) qs Perfume qs 3-Benzophenone 5.00 Example 12 Liquid make-up Wt .-% Ceteareth-6 (reaction product of fatty alcohol and ethylene oxide) and stearyl alcohol 7.00 Ceteareth-25 5.00 dimethicone 5.00 cetearyl 8.00 macadamia nut oil 5.00 propylene glycol 5.00 water 53,00 Sicovit White E 171 8.00 Sicomet Braun 70 13E 3717 1.00 Lipoic acid (> 98% ee) qs Perfume qs 3-Benzophenone 5.00 Example 13 sun-care oil Wt .-% cetearyl 40,00 Caprylic / capric triglycerides 28.70 Evening primrose oil 3.00 macadamia nut oil 5.00 isopropyl palmitate 5.00 dimethicone 3.00 octyl 8.00 octocrylene 5.00 3-Benzophenone 2.00 phytantriol 0.10 Lipoic acid (> 98% ee) qs tocopheryl acetate 0.20 Perfume qs Example 14 Facial Deep Cleaner Wt .-% water 65.60 cocoamidopropyl 5.00 Sodium cocoate, hydrolyzed animal protein 8.00 Ethoxylated hydrogenated castor oil (40 EO) 2.00 Polyquaternium-44 7.70 Bisabolol rac. 0.20 panthenol 1.00 Perfume 0.50 hydroxyethyl 2.00 Lipoic acid (> 98% ee) qs propylene glycol 5.00 jojoba 3.00 Example 15 Conditioner Wt .-% Ceteareth-6 and stearyl alcohol 2.00 Ceteareth-25 (reaction product of fatty alcohol and ethylene oxide) 1.00 cetearyl 6.00 Ceteareth-3 2.00 cetearyl 6.00 phytantriol 1.00 propylene glycol 5.00 Polyquaternium-11 5.00 panthenol 1.00 retinyl 0.50 Perfume qs Lipoic acid (> 98% ee) qs preservatives qs water 70.50 Example 16 Hair Wax Wt .-% Polyethylene glycol-6 30.00 Polyethylene glycol-75 45,00 liquid paraffin oil 0.50 Ethoxylated hydrogenated castor oil (40 EO) 1.00 glycerin 15.00 3-Benzophenone 2.00 phytantriol 0.10 Lipoic acid (> 98% ee) qs Perfume qs water 6.40 Example 17 Anti-dandruff hair tonic Wt .-% alcohol 45,00 Aloe Vera (10 times Conc.) 1.00 panthenol 1.00 tocopheryl acetate 0.50 Ethoxylated hydrogenated castor oil (40 EO) 0.50 allantoin 0.10 Hydrolyzed animal protein 1.50 1- (4-chlorophenoxy) -1- (1H-imidazolyl) -3,3-dimethyl-2-butanone 0.30 Perfume 0.10 Lipoic acid (> 98% ee) qs water 50,00 Example 18 Foot Deodorant Spray Wt .-% Ethoxylated hydrogenated castor oil (40 EO) 0.80 alcohol 20.00 farnesol 0.12 menthyl 0.08 1,2-propylene glycol 3.20 4-benzophenone 1.20 Glyceryl cocoate (7 EO) 0.80 Perfume qs Lipoic acid (> 98% ee) qs water 13.80 butane 60,00 Example 19 Hairspray Wt .-% amino methyl propanol 0.40 dimethicone 0,030 alcohol 43.67 pentane 14,20 Acrylate / acrylamide copolymer 3.40 Perfume qs Lipoic acid (> 98% ee) qs butane 2.40 isobutane 35,90

Claims (5)

Use of lipoic acid, lipoic acid derivatives or cosmetically acceptable salts thereof, each with an (R) -enantiomeric excess (ee) of at least 40%, in cosmetic preparations for rejuvenation and / or Revitalization of the skin. Use according to claim 1, wherein energizing Effects can be observed. Use according to one of the preceding claims, wherein the (R) -enantiomeric excess at least 80%, preferably at least 98%. Use according to one of the preceding claims in the form a cosmetic containing I) lipoic acid, lipoic acid derivatives or pharmaceutically acceptable salts thereof, each with an (R) -enantiomeric excess (ee) of at least 40%, II) optionally at least one another cosmetic ingredient, and III) a cosmetic acceptable carrier. Use according to claim 4, wherein the agent is the Component I in an amount of 0.001 to 30 wt .-% based on contains the total weight of the agent.